Total Synthesis of (–)-Strempeliopine
- Resource Type
- Authors
- Dale L. Boger; Xianhuang Zeng
- Source
- J Am Chem Soc
- Subject
- Indole test
Strempeliopine
Chemistry
Molecular Conformation
Iminium
Total synthesis
Stereoisomerism
General Chemistry
Biochemistry
Radical cyclization
Catalysis
Article
Ion
Indole Alkaloids
Single electron
Colloid and Surface Chemistry
Cyclization
Polymer chemistry
- Language
- English
A total synthesis of (–)-strempeliopine is disclosed that enlists a powerful SmI(2)-mediated and BF(3)•OEt(2)-initiated dearomative transannular radical cyclization onto an indole by an N-acyl α-aminoalkyl radical derived by single electron reduction of an in situ generated iminium ion for formation of a quaternary center and the strategic C19–C2 bond distinguishing its core structure.